Hydrochloric Acid → 7-bromo-9h-fluoren-2-ol

HRID 2416353Notes

Reaction equation

HRID 2416353 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([O:15]C(=O)C)=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[OH-].[Li+].Cl>C(O)CO>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([OH:15])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 22630262HCID 22630262, compound

Product 1

HCID 2635827-bromo-9h-fluoren-2-olYield 67.3%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of 2-bromo-7-acetoxyfluorene (69 g), lithium hydroxide (9 g) and ethylene glycol (350 mL) was heated for one hour while refluxing. The reaction mixture was poured into 6M-hydrochloric acid (300 mL) to terminate the reaction, and the product was extracted with ethyl acetate (350 mL). The ethyl acetate layer was washed with a saturated sodium carbonate aqueous solution and dried on anhydrous magnesium sulfate. A residue obtained by distilling the solvent off under reduced pressure was recrystallized from chloroform to obtain 2-bromo-7-hydroxyfluorene (40 g) of colorless needle crystal. The melting point was 183-184° C.

Workup

  1. temperaturewas heated for one hour
  2. temperaturewhile refluxing
  3. customto terminate
  4. customthe reaction
  5. extractionthe product was extracted with ethyl acetate (350 mL)
  6. washThe ethyl acetate layer was washed with a saturated sodium carbonate aqueous solution
  7. dry with materialdried on anhydrous magnesium sulfate
  8. customA residue obtained
  9. distillationby distilling the solvent off under reduced pressure
  10. customwas recrystallized from chloroform

Sources & evidence

ORD record
ord-2fa3b35cd4c54afcbe64b218d958f629
Source dataset
uspto-grants-2004_11
Patent number
US06824709B2

Reaction notes

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